Wed, Oct 16: Meet at the Indianapolis airport before boarding your overnight flights to Lisbon, Portugal.

Thu, Oct 17: Arrive in Lisbon, and enjoy a panoramic tour of the city and a Welcome Lunch at a local restaurant. Take in the charm of the hilly, historic Alfama neighborhood on board a Tuk Tuk (an automatic rickshaw) before transferring to your well-appointed hotel, conveniently located near the city center, for the next three nights. (Meals: Lunch, Dinner)

Fri, Oct 18: Everything old is new again in the Portuguese capital, which is undergoing a remarkable rebirth. Start the day with a visit to the Royal Coach Museum, the world’s best collection of gilded and wood-carved coaches of the Portuguese Renaissance and one of Lisbon’s most visited attractions. Head to the Jeronimos Monastery, which is a masterpiece of Manueline architecture — and decorated with sculptures and elaborate scrollwork. Glorious historic architecture reflects the wealth brought in during the “Age of Discovery,” when the Portuguese owned the seas, but it is also a modern center of finance and international trade. See the ornamental Belem Tower (the name comes from Bethlehem), built in the 16^th century to guard the port and housed cannons, prisoners, and royalty over the centuries. Another landmark, the 20^th-century Monument to the Discoveries, commemorates these voyagers and their founding patron, Prince Henry the Navigator. Spend the afternoon at your leisure before an exciting evening—dinner at an authentic Fado restaurant. Fado is a music genre so integral to the Portuguese culture that UNESCO recognizes it as part of the Intangible Cultural Heritage of Humanity. It’s galvanizing, exposed, and emotional, not to mention one of every visitors’ most treasured memories of Lisbon. (B,D)

Sat, Oct 19: Escape the excitement of the city, and travel back in time to the village of Sintra. Located between stunning beaches and fairytale forests—and filled with whimsical palaces, Sintra has long been an inspiration for poets, artists, and nobility. Stop before reaching the town center at the palace of Queluz, known to some as Portugal’s “Versailles”. Take a brief walking tour of quaint downtown Sintra, and tour the National Palace, with its mixture of architecture and decorative features, from Islamic tiles to Gothic details to ceilings painted with swans and magpies. Sample the local flair with an included lunch, before a short drive to the popular sun-kissed, resort town of Cascais. Spend some time on your own, walk along the beach, shop or sip a cocktail with an incredible view before returning to Lisbon. (B,L)

Sun, Oct 20: Board a motorcoach and travel north through Portugal’s picturesque countryside to Porto. En route, stop in Coimbra—Portugal’s first capital, and tour the ancient university and its lavish baroque library, the Joanina, considered one of the most beautiful in the world. After seeing a little of the town itself, which boasts Moorish and Roman architectural remnants, stop for lunch before continuing on to Porto to board the S.S. Sao Gabriel—your home for the next seven nights. (B,L,D)

Mon, Oct 21: Choose between two distinctive ways to explore Porto today: a city tour by motorcoach, or a walking tour. On the city tour, travel through medieval alleys and UNESCO-designated neighborhoods enclosed by 14^th-century walls. See the Clergios Tower, the 19^th-century Stock Exchange Palace, Porto’s austere hilltop cathedral, and Santa Catarina—the bustling pedestrian shopping street. On the walking tour, cross the upper level of the Ponte Dom Luis for one of the best views in Porto. Visit Bolhao Market to experience local delicacies and explore the Sao Bento railway station. Walk through the Clerigos Quarter to discover the stunning architecture up close before returning to the ship. The ship cruises up the Douro toward Porto Antigo this afternoon. Five famous bridges link Porto to Vila Nova da Gaia, including the graceful iron arches of Dom Luis I. Sail under all of them before entering the mouth of the Douro River. (B,L,D)

Tue, Oct 22: Your day in Regua is all about wine, which has been cultivated in the Douro River Valley since ancient Roman times. Get a crash course on the history of Port during your visit to the Douro Museum. Exhibits laid out in buildings that were once home to Port winemaker Real Companhia Velha, let you see firsthand how the process of making Port has evolved over the centuries. By sniffing vials of concentrated fragrance, you can learn to identify the many aromas that a good Port exhibits and sip some regional samples. Travel up winding roads with spectacular views and breath-taking drop-offs for an included dinner at the hilltop winery, Quinta da Avessada. Built a century ago, this quinta produces delicious Moscatels, a wine that is very popular in Portugal. (B,L,D)

Wed, Oct 23: Enjoy awe-inspiring scenery this morning as the ship cruises the upper Douro River Valley, a UNESCO World Heritage Site both because of its beauty and its remarkable history. Head ashore in Pinhao and opt to visit the Archaeological Park of the Coa Valley to discover an astonishing collection of prehistoric carvings ranging from the Epipaleolithic and Bronze ages to the 17^th century. Or choose to explore the comparatively “modern” Castelo Rodrigo, a medieval castle standing at the heart of the still-lively village. The view from the top is incredible and the village is a charming place to ramble, relax, and replenish. Later in the day, the ship will drift down the Douro toward Porto to dock for the last two nights. (B,L,D)

Thu, Oct 24: Today, visit the historic university town of Salamanca, Spain, where Columbus sought advice before sailing west in search of a new route to the Indies. Called the Golden City for its tawny sandstone buildings, the city boasts an abundance of beautiful churches — including the Old Cathedral, which dates to the 12^th century. Walk through Plaza Mayor, lined with wonderful baroque buildings, to the university founded by Alfonso IX in 1218. Visit Salamanca’s food hall and taste some of Spain’s best cheeses and meats before free time to browse the shops on Rua Mayor. (B,L,D)

Fri, Oct 25: Feel the centuries fall away as the ship winds its way through the pristine, dramatic, UNESCO-protected landscapes of the Douro River Valley. A tiny village surrounded by mountains, Barca d’Alva is your base for today’s adventures. Choose between two excursions: a port wine estate tour with a tasting, or a vineyard hike with a tasting at a local quinta. The ship docks near the Spanish border this evening. (B,L,D)

Sat, Oct 26: Enjoy a city tour of historic Guimaraes (where Portugal was born), one of Porto’s oldest neighborhoods. In Guimaraes, explore the wonderfully well-preserved Old Town, with its unique architecture (houses here combine granite with half-timbering) and charming little plazas. Rove with your guide from the castle that overlooks the town toward the beautiful main square, the Largo da Oliveira, and to the splendid Monastery and Church of Our Lady of Oliveira and the 14th-century Gothic Padrao do Salado. In the evening, enjoy a special Farewell Dinner. (B,L,D)

Sun, Oct 27: Disembark in Porto and transfer to Lisbon with sightseeing stops along the way. Overnight Lisbon. (B,L)

Mon, Oct 28: After breakfast in the hotel, transfer to the airport for your flights home. (B)